Triazoles



Patented Mar. 4, 1941 UNITED STATES PATENT OFFICE in Anhalt, Germany,signments, to General assignors, by mesne as- Aniline & FilmCorporation, New York, N. Y., a corporation of Delaware No Drawing.Application October 20, 1938, Serial No. 236,030. In Germany October 28,1937 7 Claims.

The present invention relates to nitrogeneous condensation products, themanufacture thereof, and to a process of improving textiles. Specificdetails may be seen from the specification following hereafter.

It has been found that fatty acids containing more than 10 carbon atomscan in a simple manner be transformed into bases by melting them withamino-guanidine. For this purpose, the amino-guanidine may, forinstance, be introduced into the molten fatty acid at a raisedtemperature (about 140 0.). Water vapor escapes, its amount beingequivalent to 2 mols in case 1 mol of fatty acid has been caused toreact with 1 mol of amino-guanidine.

In this condensation, there is probably formed with ring-closure aderivative of the aminotriazole, as is shown for stearic acid in thefollowing formulae:

Instead of the free base there is preferably used one of its salts. Thecarbonate, for instance, is especially suitable in view of the highvolatility of carbonic acid. If salts of less volatile acids, forinstance, the chlorides, are used, it is preferable to bind the acid,after heating for a short time, by introduction of sodium carbonate orof other alkalies.

The temperature required for the condensation depends upon the nature ofthe components entering into reaction and upon the conditions ofreaction. In general, it is necessary to apply temperatures above C. toabout 200 0., a temperature of about C. is preferred. The water formedas a reaction product may also be removed by azeotropic distillation,for instance, by means of benzene.

The following examples illustrate the invention, the parts being byWeight:

Example 1.136 parts of amino-guanidine carbonate are slowly introduced,at 140 0., while stirring, into 284 parts of molten stearic acid.

The melt, which initially begins to foam, becomes gradually clear,carbon dioxide and water being split 01f. After 36 parts of water havebeen split off, the reaction is interrupted. The melt which solidifiesto a wax-like body is soluble in dilute acids, such as hydrochloricacid.

The product may be purified by boiling it with a dilute sodium carbonatesolution in order to eliminate small amounts of unaltered parentmaterial, which may perhaps be present.

Instead of stearic acid, there may also be used with the same successcoconut oil fatty acid, oleic acid, ricinoleic acid or also halogenatedfatty acids and fatty acids having a branched chain.

The amines thus obtained are soluble in dilute acids and they remainstable even if their solution in such acids is heated for a prolongedperiod of time. They display valuable properties as textile adjuvants.

Example 2.A rayon skein having a weight of 100 grams is handled, forabout 30 minutes, at 40 C. in 1000 cm. of a bath containing 0.1 gram ofheptadecylaminotriazole hydrochloride. After thorough rinsing anddrying, the silk is very soft to the touch.

The corresponding N-alkyl or N-hydroxyalkyl derivatives may be used withthe same success.

The new softening agents bring about practically no change of shade ondyed skeins or fabrics. As some of them give rise to the formation ofdifiiculty soluble sulfates, it is preferable to avoid any separation inflakes-in the case of water containing sulfates-by operating in thepresence of protective colloids. The above-described textile processingis suitable not only for pure rayon of. the most varied kinds, but alsofor mixed fabrics as well as for natural fibers of vegetable or animalorigin, such as wool and linen.

The invention is not limited to the specific details described, forobvious modifications may occur to a person skilled in the art.

What we claim is:

1. Triazoles of the general formula R stands for alkyl with more than 9carbon atoms, being soluble in dilute acids and being textile adjuvants.

2. The process of producing triazoles which comprises condensing dryamino-guanidine of the formula NH.NH:

HN=C

with an unsubstituted fatty acid containing more than 10 carbon atoms byheating to a temperature not exceeding substantially 200 C. until in oneoperation 2 mols of water are split ofi.

3. The process of producing triazoles which comprises condensing a drysalt of amino-guanidine with an unsubstituted fatty acid containing morethan 10 carbon atoms by heating to a temuntil in one operation 2 mols ofwater are split off.

5. The process of producing triazoles which comprises condensing a. drysalt of amino-guanidine with stearic acid by heating to a temperaturenot exceeding substantially 200 C. until in one operation 2 mols ofwater are'split off.

6. The process of producing triazoles which comprises condensing a drysalt of amino-guanidine with oleic acid by heating to a temperature notexceeding substantially 200 C. until in one operation 2 mols of waterare split oil.

7. The process of producing triazoles which comprises condensing a drysalt of amino-guanidine with coconut oil fatty acid by heating to atemperature not exceeding substantially 200 C. until in one operation 2mols of water are split off.

KARL BRODERSEN.

MATHIAS QUAEDVLIEG.

